Reaction of 4-methoxy-4-(1-methylethenyl)-2-cyclobutenone derivatives with 2-lithiopropene and alpha-lithiostyrene: synthesis of eight-membered ring carbocycles

Zora, Metin
Yucel, B
2-Alkyl- or phenyl-substituted 4-methoxy-4-(1-methylethenyl)-2-cyclobutenones react with 2-lithiopropene or alpha-lithiostyrene to produce 4-methoxy-2,4-cyclooctadienones in moderate yield, accompanied by varying amounts of 4-methoxy-4-(1-methylethenyl)-2-cyclohexenones. The reaction is general for 2-alkyl substituted 4-methoxy-4-(1-methylethenyl)-2-cyclobutenones.


Reaction of ferrocenylcarbene complexes of Cr, Mo and W with alkynes: Synthesis of ferrocenylcyclobutenones, ferrocenylfurans and ferrocenylketoesters
Zora, Metin (Elsevier BV, 2001-07-09)
Ferrocenylcarbene complexes of Cr, Mo and W react with alkynes to produce cyclobutenones, furans and/or ketoesters. The reaction is quite sensitive to the substituents of the alkyne, regardless of the identity of the metal. Cyclobutenones are formed only in the reactions of diphenylacetylene, a rare occurrence for metal carbene complexes. Ketoesters are secondary reaction products and result From oxidation of furan derivatives during the course of the reaction and/or silica-gel chromatography.
Reaction of Metal-Carbene Complexes with Cyclobutenediones: The First General C-C Bond Insertion Reaction for Fischer Carbene Complexes
Zora, Metin (American Chemical Society (ACS), 1993-01-01)
Alkylcarbene-chromium complexes react with cyclobutenediones to give 2-alkoxy-4-cyclopentene-1,3-diones in moderate yield, accompanied by varying amounts of 4-cyclopentene-1,3-dione derivatives which result from reduction of the initial product by the chromium byproduct. The reaction is general for a variety of cyclobutenedione derivatives with alkoxy, alkyl, or aryl substituents. The major products of the reaction between arylcarbene complexes and cyclobutenediones are 5-alkylidenefuranone derivatives. A m...
Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones
Zora, Metin; Bueyuekguengoer, Orhan (Elsevier BV, 2007-05-07)
The coupling of ferrocenyl alkynes with cyclopropylcarbene-chromium complex leads to ferrocenyl-substituted 2-cyclopentenones with or without a hydroxy substituent, namely 4-cyclopentene-1,3-diones, 2-cyclobutenones, and alpha, beta-unsaturated aldehydes in varying amounts. The reaction initially produces a cyclopentadienone intermediate, then to the double bond of which, bearing a ferrocenyl group, addition of water occurs to afford hydroxy-substituted 2-cyclopentenones. In all the products, the hydroxy gr...
Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary alpha-hydroxy phosphonates
Seven, Ozlem; Polat-Cakir, Sidika; Hossain, Md. Shakhawoat; Emrullahoglu, Mustafa; Demir, Ayhan Sıtkı (Elsevier BV, 2011-05-13)
The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of alpha-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary alpha-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 degrees C gave the secondary alpha-hydroxy phosphonates, while at -100 degrees C they affo...
Synthesis, Characterization, and Thermal Properties of Alkyl-Functional Naphthoxazines
UYAR, Tamer; Hacaloğlu, Jale; Ishida, Hatsuo (2013-02-15)
A series of alkyl-functional naphthoxazine resins having various alkyl chain lengths from C1 to C18 are synthesized with a high yield and high purity by the reactions of 1,5-dihydroxynaphthalene, formaldehyde, and aliphatic amines. The proposed chemical structures of the naphthoxazines are confirmed by high-resolution mass spectrometry, H-1 nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and pyrolysis mass spectrometry studies. The alkyl-functional naphthoxazines have shown...
Citation Formats
M. Zora and B. Yucel, “Reaction of 4-methoxy-4-(1-methylethenyl)-2-cyclobutenone derivatives with 2-lithiopropene and alpha-lithiostyrene: synthesis of eight-membered ring carbocycles,” TETRAHEDRON LETTERS, pp. 7111–7114, 2000, Accessed: 00, 2020. [Online]. Available: